Triethylamine → HCID 44469673, Verbindung

HRID 1626347Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626347
[C:1]([C:3]1[CH:27]=[CH:26][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=3)=[O:16])[CH2:10][CH2:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.CN(C(ON1N=N[C:45]2[CH:46]=[CH:47][CH:48]=[N:49][C:44]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:59]([O:61][C:62]1[CH:74]=[CH:73][C:65]([CH2:66]C2CCNCC2)=[CH:64][CH:63]=1)[CH3:60]>CN(C)C=O.O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:16])[C:17]3[CH:18]=[CH:19][C:20]([C:21]([CH:46]4[CH2:45][CH2:44][N:49]([CH2:66][C:65]5[CH:73]=[CH:74][C:62]([O:61][CH2:59][CH3:60])=[CH:63][CH:64]=5)[CH2:48][CH2:47]4)=[O:23])=[CH:24][CH:25]=3)[CH2:10][CH2:9]2)=[CH:26][CH:27]=1)#[N:2]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 47782654-(4-ethoxybenzyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69008872HCID 69008872, Verbindung

Produkt 1

HCID 44469673HCID 44469673, VerbindungAusbeute 450,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of 4-(1-(4-cyanobenzyl)piperidin-4-ylcarbamoyl)benzoic acid (100 mg, 0.275 mmol) in anhydrous N,N-dimethylformamide (3 mL) was added triethylamine (84 μl, 0.825 mmol), HATU (115 mg, 0.3 mmol), and 4-(4-ethoxybenzyl)piperidine (61 mg, 0.275 mmol). The mixture was stirred at room temperature overnight and then poured into water. The resulting solids were collected by filtration, purified by column chromatography to yield 0.7 g (55%) of N-(1-(4-cyanobenzyl)piperidin-4-yl)-4-(1-(4-ethoxybenzyl)piperidine-4-carbonyl)benzamide (compound 27) as an off white solid. 1H-NMR (CDCl3, 300 MHz): δ 7.761 (d, 2H), 7.600 (m, 2H), 7.434 (m, 4H), 7.022 (d, 2H), 6.812 (d, 2H), 6.022 (d, 1H), 4.658 (m, 1H), 3.994 (dd, 2H), 3.569 (m, 3H), 2.885 (m, 4H), 2.505 (m, 2H), 2.227 (m, 2H), 2.049 (m, 2H), 1.639 (m, 6H), 1.405 (m, 3H); LCMS (m/z): 565 (MH+).

Aufarbeitung

  1. filtrationThe resulting solids were collected by filtration
  2. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d9733cebe27e45028df77ff9a49b2534
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785449B2

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